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Pyridine pyrazole copper [i] complex organic vapor luminescent color-changing material and preparation method

A technology of copper pyridine pyrazole and organic vapor, which is applied in the direction of color-changing fluorescent materials, copper organic compounds, chemical instruments and methods, etc., can solve the problems of tight source of raw materials, scarce content, few literature reports, etc., and achieve fast and efficient organic vapor luminescence. The effect of color changing properties

Active Publication Date: 2017-12-12
JIANGXI UNIV OF SCI & TECH
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Problems solved by technology

The transition metal elements of the fifth and sixth periods (except for a few metal elements of the first and second subgroups) are scarce in the earth’s crust and are difficult to mine, so the cost of using luminescent complexes based on such noble metal elements is relatively high. Moreover, large-scale application will also bring about the problem of shortage of raw material sources.
However, there are few reports in the literature on the synthesis of monovalent copper dinuclear complex luminescent and color-changing materials using nitrogen heterocyclic multidentate chelating ligands and organic bisphosphine ligands, especially monovalent copper complex organic vapor luminescent color-changing materials.
[0005] Using pyridinepyrazole chelating ligand 5-trifluoromethyl-3-[2-pyridyl]pyrazole and organic bisphosphine ligand as auxiliary ligand, the technology of synthesizing monovalent copper complex organic vapor luminescent color-changing new materials , there is no public report in the literature

Method used

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  • Pyridine pyrazole copper [i] complex organic vapor luminescent color-changing material and preparation method
  • Pyridine pyrazole copper [i] complex organic vapor luminescent color-changing material and preparation method
  • Pyridine pyrazole copper [i] complex organic vapor luminescent color-changing material and preparation method

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Experimental program
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Effect test

Embodiment 1

[0030] Under an argon atmosphere, [Cu[MeCN] 4 ][ClO 4 ] (21.6mg, 0.066mmol), 1,2-bis[diphenylphosphine]ethane (26.4mg, 0.066mmol) and 5-trifluoromethyl-3-[2-pyridyl]pyrazole (14.1mg , 0.066mmol) in 10mL of dichloromethane and stirred at room temperature for 3 hours, then added sodium hydroxide (2.7mg, 0.067mmol) to the reaction solution, continued to stir and reacted for 1 hour at room temperature, and then evaporated the solvent with a rotary evaporator Dry and recrystallize with a mixed solvent of dichloromethane (1 mL)-petroleum ether (10 mL) [volume ratio 1:10]. The light yellow crystalline product obtained by filtration and recrystallization was washed with 10 mL of ether for 3-4 times, and vacuum-dried to obtain a light yellow solid product——pyridine pyrazole copper [I] complex organic vapor luminescent color-changing material (35.1 mg, 0.026 mmol ), the yield is 79%.

[0031] Elemental analysis calculated value (C 70 h 58 Cu 2 f 6 N 6 P 4 ) as (%): C 62.36, H 4...

Embodiment 2

[0035] Under argon atmosphere, copper perchlorate hexahydrate [Cu[ClO 4 ] 2 ·6H 2 O] (11.9mg, 0.032mmol) and excess copper powder (18.8mg, 0.296mmol) were stirred in 5mL acetonitrile for 30 minutes at room temperature, then added 1,2-bis[diphenylphosphine]ethane (25.6mg, 0.064 mmol) in 10 mL of dichloromethane solution, continue stirring for 1 hour, then add 5-trifluoromethyl-3-[2-pyridyl] pyrazole ligand (13.7 mg, 0.064 mmol), and continue stirring for 2 hours at room temperature , Add sodium hydroxide (2.6mg, 0.065mmol) to the reaction solution, and continue to stir the reaction at room temperature for 1 hour. ) mixed solvent [volume ratio of 1:10] for recrystallization. The light yellow crystalline product obtained by filtration and recrystallization was washed with 10 mL of ether for 3-4 times, and vacuum-dried to obtain a light yellow solid product——pyridine pyrazole copper [I] complex organic vapor luminescent color-changing material (32.4 mg, 0.024 mmol ), the yield...

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Abstract

The invention relates to a synthetic technology for an organic vapor luminescent off-color material, and particularly to an organic vapor luminescent off-color material of a dinuclear copper [I] complex containing pyridine pyrazole chelate ligands and a preparation method thereof. According to the invention, the pyridine pyrazole chelate ligands (5-trifluoromethyl-3-[2-pyridyl]pyrazol [pyfpzH for short]) and organic diphosphonic auxiliary ligands (1,2-bis[diphenylphosphine]ethane [dppe for short]) are used to prepare an organic vapor luminescent off-color material [Cu2[pyfpz]2[dppe]2] of a pyridine pyrazole dinuclear copper [I] complex. At normal temperature, the maximum value of the solid state luminescent wavelength of the pyridine pyrazole dinuclear copper [1] complex is 493nm, the luminescent lifetime is 49 microseconds, the luminescent quantum efficiency is 71%, and a fast efficient organic vapor luminescent off-color property to dichloromethane vapor is shown.

Description

technical field [0001] The invention relates to the synthesis technology of new organic vapor luminescent and color-changing materials, in particular to a binuclear copper [I] complex organic vapor luminescent and color-changing material containing pyridine and pyrazole chelating ligands and a preparation method thereof. Background technique [0002] Due to the influence of heavy atom effect and strong spin-orbit coupling, transition metal light-emitting complexes can theoretically utilize all singlet and triplet energy, and the luminous efficiency can be greatly improved. At present, transition metal luminescent complexes mainly focus on the fifth and sixth periods, especially transition metals of group VIII, while ruthenium, osmium, iridium and platinum occupy the center of current research. The transition metal elements of the fifth and sixth periods (except for a few metal elements of the first and second subgroups) are scarce in the earth’s crust and are difficult to mi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C09K9/02
CPCC07F1/005C07F1/08C09K9/02C09K2211/1029C09K2211/1044C09K2211/188
Inventor 陈景林罗燕生何丽华廖金生刘遂军温和瑞
Owner JIANGXI UNIV OF SCI & TECH
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